I think everybody has an opinion on anal – it’s hard to be neutral about it. Something that has the potential to be both seriously pleasurable or seriously painful and which takes a bit more skill than your average vaginal penetration. There’s lots of different types but today I’m thinking about the kind I’ve experienced with penis-owners.
I remember pretty vividly the first time someone put a finger into my anus about 13 years ago. I was shocked, uncomfortable, embarrassed and awkward. Surprise butt sex is never good. However, I was also very interested by the pleasurable sensations that this produced and was pretty motivated to explore what I could do on my own. Somehow this led to a long masturbation session involving a Rampant Rabbit vibrator in my bottom, interrupted by irritating housemates knocking on the door intermittently demanding to borrow my guitar, as though I were in some kind of farcial comedy sketch. It became a regular thing (when the housemates were away), but I didn’t have a penis in there until five years after.
The first time I had that form of anal sex, we did everything wrong. We knew we were doing everything wrong. I was in love, horny, seeing my long-distance boyfriend who I felt the very great need to have sex with. I was on my period (and hadn’t at this point graduated to period sex). We had no lube, but we did have a condom that claimed to have extra lube on it. I identified as a lesbian with a giant crush on this one guy. We decided we might as well give it a go. It hurt very little and felt very good.
This brings me to my first point. When you practise the craft of anal, some penis-owners are more blessed than others. Some penises seem to be the exact right shape and size to avoid pain and to feel pretty good. Of course, it’s always possible if someone owns the wrong kind of penis, that they could strap on the other kind when appropriate (if they are into that).
A few years later, I experienced the other kind of penises. The kind that for me have the edge when it comes to vaginal penetration, but are fairly intimidating when it comes to anal. Both length and girth are factors.
One element in the craft of anal, when it comes to larger penises, is eroticising the unavoidable extra pain. Yes, there is building up slowly, yes there is lube, but there is going to be discomfort and some pain. If you’re the sort of person that can find some form of pain during sex enjoyable, this is your best angle. Or equally if you’re not actually masochistic but enjoy pleasing sadists, that outlook can help you with the right partner. To use either of these approaches you have the best chance of success if your partner knows how you feel and what words, phrases or additional signals will get you going.
The other challenges in anal sex besides the pain are feelings of being dirty, humiliated, embarrassed or ashamed. A lot of those feelings are good to eroticise too – you might choose to play up or play down any one of these aspects to tailor your experience to what you can enjoy.
I enjoy many of the aspects of anal but because it’s so intense I don’t seek it out that often and generally only with a partner I’m very emotionally close to so I can trust them to handle some of the more submissive feelings that this kind of sex gives me.
There are times though when it all seems to go right and it magically doesn’t hurt at all. There’s probably a different ‘recipe’ for each person for this, but I like using a mixture of clitoral stimulation (but not to orgasm because that seems to clamp everything down again), buttplugs and lube.